TW200922938A - Oxaspirocyclic spiro-substituted tetramic acid and tetronic acid derivatives - Google Patents

Info

Publication number

TW200922938A

TW200922938A TW097129156A TW97129156A TW200922938A TW 200922938 A TW200922938 A TW 200922938A TW 097129156 A TW097129156 A TW 097129156A TW 97129156 A TW97129156 A TW 97129156A TW 200922938 A TW200922938 A TW 200922938A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

alkoxy

formula

compound

Prior art date

2007-08-02

Links

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• RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical class OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 title abstract description 6
• PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical class CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 280
• 239000000203 mixture Substances 0.000 claims abstract description 134
• 238000000034 method Methods 0.000 claims abstract description 114
• 239000002253 acid Substances 0.000 claims abstract description 83
• 238000002360 preparation method Methods 0.000 claims abstract description 63
• 230000000694 effects Effects 0.000 claims abstract description 42
• 230000002363 herbicidal effect Effects 0.000 claims abstract description 38
• 239000004009 herbicide Substances 0.000 claims abstract description 33
• 230000001965 increasing effect Effects 0.000 claims abstract description 8
• 239000000460 chlorine Substances 0.000 claims description 284
• -1 -alkyl Chemical group 0.000 claims description 196
• 239000001257 hydrogen Substances 0.000 claims description 106
• 229910052739 hydrogen Inorganic materials 0.000 claims description 106
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 229910052801 chlorine Inorganic materials 0.000 claims description 88
• 150000002431 hydrogen Chemical class 0.000 claims description 88
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 82
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
• 239000011737 fluorine Substances 0.000 claims description 78
• 229910052731 fluorine Inorganic materials 0.000 claims description 78
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
• 125000003545 alkoxy group Chemical group 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 56
• 229910052794 bromium Inorganic materials 0.000 claims description 56
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 55
• 239000007789 gas Substances 0.000 claims description 54
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 54
• 238000012360 testing method Methods 0.000 claims description 51
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 50
• 125000001153 fluoro group Chemical group F* 0.000 claims description 50
• 229910052760 oxygen Inorganic materials 0.000 claims description 49
• 239000001301 oxygen Substances 0.000 claims description 49
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 48
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 48
• 125000005843 halogen group Chemical group 0.000 claims description 48
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 46
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
• 239000003085 diluting agent Substances 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• 239000011593 sulfur Substances 0.000 claims description 38
• 238000006243 chemical reaction Methods 0.000 claims description 36
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 36
• 239000003795 chemical substances by application Substances 0.000 claims description 34
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 34
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
• 239000002904 solvent Substances 0.000 claims description 34
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
• 239000002689 soil Substances 0.000 claims description 31
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 239000000126 substance Substances 0.000 claims description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
• 150000001412 amines Chemical class 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
• 239000011230 binding agent Substances 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000003277 amino group Chemical group 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 14
• 235000021419 vinegar Nutrition 0.000 claims description 14
• 239000005864 Sulphur Substances 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 239000002184 metal Substances 0.000 claims description 13
• 239000000052 vinegar Substances 0.000 claims description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 238000001784 detoxification Methods 0.000 claims description 12
• 239000007788 liquid Substances 0.000 claims description 12
• 229910052751 metal Inorganic materials 0.000 claims description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
• 150000001721 carbon Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 239000003054 catalyst Substances 0.000 claims description 10
• 125000006612 decyloxy group Chemical group 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 239000004305 biphenyl Substances 0.000 claims description 9
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 150000002148 esters Chemical class 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 9
• 125000001188 haloalkyl group Chemical group 0.000 claims description 8
• 229910021645 metal ion Inorganic materials 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
• 241000607479 Yersinia pestis Species 0.000 claims description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 235000010290 biphenyl Nutrition 0.000 claims description 7
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 238000005507 spraying Methods 0.000 claims description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
• 150000002923 oximes Chemical class 0.000 claims description 6
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 6
• 239000007921 spray Substances 0.000 claims description 6
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000006267 biphenyl group Chemical group 0.000 claims description 5
• 239000004202 carbamide Substances 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
• MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 4
• YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 4
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 4
• HJSRGOVAIOPERP-UHFFFAOYSA-N 5-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=CC2=N1 HJSRGOVAIOPERP-UHFFFAOYSA-N 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 238000009833 condensation Methods 0.000 claims description 4
• 230000005494 condensation Effects 0.000 claims description 4
• OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 4
• 125000005567 fluorenylene group Chemical group 0.000 claims description 4
• 125000001475 halogen functional group Chemical group 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 4
• 150000002429 hydrazines Chemical class 0.000 claims description 4
• MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
• 235000013336 milk Nutrition 0.000 claims description 4
• 239000008267 milk Substances 0.000 claims description 4
• 210000004080 milk Anatomy 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
• 230000000149 penetrating effect Effects 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 239000004094 surface-active agent Substances 0.000 claims description 4
• ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 claims description 3
• 239000002794 2,4-DB Substances 0.000 claims description 3
• VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 3
• 229910002651 NO3 Inorganic materials 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 229910052698 phosphorus Inorganic materials 0.000 claims description 3
• 239000011574 phosphorus Substances 0.000 claims description 3
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 2
• SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims description 2
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 2
• WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 2
• WZROSPHFTWMIGM-UHFFFAOYSA-N 2-decoxyacetic acid Chemical compound CCCCCCCCCCOCC(O)=O WZROSPHFTWMIGM-UHFFFAOYSA-N 0.000 claims description 2
• ZAYKVYVNMLEAMI-UHFFFAOYSA-N 4-(carboxymethyl)-2,3-dihydrochromene-4-carboxylic acid Chemical compound C1=CC=C2C(CC(=O)O)(C(O)=O)CCOC2=C1 ZAYKVYVNMLEAMI-UHFFFAOYSA-N 0.000 claims description 2
• PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 2
• FGTPQGXNZZZONI-UHFFFAOYSA-N ClC1(N=C2C=CC=CC2=C1)Cl Chemical compound ClC1(N=C2C=CC=CC2=C1)Cl FGTPQGXNZZZONI-UHFFFAOYSA-N 0.000 claims description 2
• 239000005504 Dicamba Substances 0.000 claims description 2
• UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 claims description 2
• 101100258315 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-1 gene Proteins 0.000 claims description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 150000001449 anionic compounds Chemical class 0.000 claims description 2
• MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 2
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• SQFPMCDRPGJOQH-UHFFFAOYSA-N ethyl 5-(4-fluorophenyl)-5-phenyl-4h-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC(F)=CC=1)C1=CC=CC=C1 SQFPMCDRPGJOQH-UHFFFAOYSA-N 0.000 claims description 2
• 210000004907 gland Anatomy 0.000 claims description 2
• 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 2
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
• 229910001412 inorganic anion Inorganic materials 0.000 claims description 2
• 150000002540 isothiocyanates Chemical class 0.000 claims description 2
• 150000002736 metal compounds Chemical class 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 150000002891 organic anions Chemical class 0.000 claims description 2
• 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
• HDBQZGJWHMCXIL-UHFFFAOYSA-N 3,7-dihydropurine-2-thione Chemical compound SC1=NC=C2NC=NC2=N1 HDBQZGJWHMCXIL-UHFFFAOYSA-N 0.000 claims 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
• NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims 2
• XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
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